Dare
by wedontstandachance
Summary: DESTIEL Castiel asks Dean out as a dare, and doesn't expect him to say yes. He feels pretty guilty about it.


It all started with a stupid game of dare.

It was a yet another boring, Thursday afternoon in a long string of boring afternoons that teenagers all had to suffer through during winter break. Christmas had been the week before, and there were still a few more days before it would be time yet again to head back to class. Castiel and Charlie, having exhausted every other outlet of entertainment available to them, had nothing better to do than to sit on a park bench and people watch. It was something they did sometimes to pass the time when there were no new movies playing that they wanted to see, or when they'd grown so tired of staring at the same four walls of one of their bedrooms that they'd needed to get out and get some fresh air and a change of scenery.

They'd started the game about an hour before. They had been just sitting there, sipping their coffees and chatting. And then during a brief lull in their conversation Charlie had glanced to her right, and then back at Castiel and said, "I dare you to try and catch that pigeon."

Castiel followed her gaze to the lone bird pecking around on the ground a few feet away and shrugged. "Alright," he answered.

Because why not? It wasn't like he had anything better to do anyway. And he wasn't usually one to back down from a challenge. He was the kind of person who took dares very seriously. Double dog dares had been _monumentally_ important to him as a child, and _don't_ even get him started on triple dog dares. He may have been eighteen now, but that was one thing that he never really grew out of. Much to his mother's displeasure. But not many things pleased her as it was.

Charlie seemed kind of surprised for a moment when he'd agreed, but rolled with it anyway. It had been her idea after all.

Wordlessly, Castiel took one more sip, and then handed over his half-finished coffee for Charlie to hold for safe-keeping while he was on his pigeon-capturing mission. He stood up and straightened his jacket and scarf. Charlie saluted him for good luck, and he gave her a curt nod in return.

He started inching away from the bench slowly, trying not to startle the bird. He was a man on a mission of the utmost importance. He was focused, he was adept, and he was zeroed in on that bird—(he may have been taking this a bit too seriously).

The poor, unsuspecting pigeon barely even registered his presence—having lost its fear of humans somewhere along the way, until he was about a foot away. Then all at once, the bird stopped pecking and abruptly shifted its head up to lock eyes with him. They had a brief, intense stare down, and then Castiel lunged. The pigeon moved at the same time that he did, scurrying a few inches to the left, before lifting its wings for flight. Castiel dove at it, hands reaching, and was met with a face full of flapping wings and feathers as he hit the ground. Hard. Needless to say, his mission had failed. He had not caught the bird; which, when you think about it, was unsurprising.

He stared up from his spot on the concrete and watched as the bird soared up into the air and landed in a tree a few hundred feet away, looking no worse for wear. Behind him he could hear Charlie's cackling. He rolled over and glared at her. She was holding up her cellphone and pointing it directly at him, having no doubt taped the whole thing. It would most likely end up on all of her various social media accounts sometime later. Not that Castiel would ever see it. Technology wasn't really his forte. Ask him a question about anatomy or cell structure and he could talk your ear off for hours. Hand him an iPhone and he'd barely be able to send a text message. But everyone had their strengths and weaknesses and he'd grown used to it; even if most of his weaknesses arose from modern day technology. As long as he understood how to use the medical equipment that he'd need for his future as a doctor, then nothing else really mattered.

Around them, people were staring at him strangely, probably thinking that he was some weird, pigeon-harassing menace. Or on drugs. Take your pick.

He stood up from the ground and brushed himself off with as much dignity as he could muster, and walked the few feet back to Charlie. He took his seat regally, and reached for his coffee. She handed it to him without a word, biting down on her lip to suppress a giggle.

He took a long pull from his drink, and then said, "I dare you to climb that tree over there."

It went back and forth like that from there.

"I dare you to do a cartwheel down the pathway."

"I dare you to sing the National Anthem in its entirety with your hand over your heart while standing on this bench."

"I dare you to hug that guy over there."

"I dare _you_ to hug that guy over there."

Back and forth, back and forth. Until Charlie delivered what would become the final dare of the day.

"I dare you to ask out the next guy that walks by."

Castiel groaned. "Even if he's old and gross?"

Charlie grinned wickedly. "_Especially_ if he's old and gross."

Castiel sighed. "Fine," he agreed.

Because again, why not? He hadn't turned down a dare yet today, and he was feeling adventurous. Plus, he hadn't asked anyone out since he and Meg had broken up, and that had been months ago. He could use the practice. Even if it was all a joke. Honestly, the guy—whoever he ended up being, probably wouldn't even stop walking or pay him any mind at all. Anyone would be able to tell that it was a joke right away. Stupid teenagers just doing it for a laugh. Even Castiel would be able to tell if he was on the receiving end, and he was as socially inept as they came. And really, who just asked a random person out in the park without knowing them anyway? Whoever it was would know right away that he was kidding. Then he and Charlie could have a good laugh over it, and they would go on with their game.

The next ten minutes passed with no male presence whatsoever. There were moms with strollers, old ladies with their walkers, a group of teenage girls; but absolutely no men. None, nada, zilch. Charlie sat next to him growing more and more agitated with each passing minute.

"Oh _come _on," she complained. "We can't move on with the game until you finish this one. Where the hell is all the testosterone up in this place? Geez!" She paused for a moment in consideration. "Huh," she said with a chuckle. "Never thought you'd hear me say that. Am I right?"

He had to agree—on both accounts—but really he just wanted some guy to cross his path so he could just ask him out and get it over with. He was starting to get bored again.

Castiel was about to reply when Charlie punched him in the shoulder, nearly knocking him off the bench. "Oh look! Here's one now!" she cried in delight.

And she was right. There was a guy currently walking down the path headed straight towards them. He had his headphones in, and his head was angled down looking at his phone. He was wearing a pair of fitted jeans, and a worn leather jacket zippered all the way up to his neck to try and defend against the winter chill in the air. As he got closer, Castiel could tell right away that he was attractive. No scratch that. Not just attractive, he was _gorgeous_.

He swallowed hard, suddenly nervous. It was one thing if it was some little old man, or some middle aged guy who would just brush him off as some stupid kid. But this guy looked to be about his age. And he was good looking. _Oh god_ he was good looking. It suddenly threw an unexpected wrench into the dare.

Charlie waved a hand in front of his face. "Hello, Earth to Castiel. Come in, Castiel. Guy at twelve o' clock. Let's get this show on the road!" He opened his mouth to tell her that he couldn't do it—wouldn't do it, because he was suddenly a big fat chicken who was terrified of even speaking to someone so attractive, let alone getting turned down by him. Even if it was just a dare. But then Charlie pushed him forward, propelling him out of his seat. And right into the guys path.

He was about ten feet away now, closing in quickly. Castiel had mere seconds left before he lost his window. The guy must have noticed him standing in his way because he began angling away so he could walk around him. Castiel briefly considered just sitting back down and letting him pass, but he stopped himself. He was Castiel freaking Novak. The guy who lived and breathed for a challenge. He had to be like that growing up in a house with Gabriel. And if he'd learned anything from his childhood, he did not turn down a dare. Never. No matter how hot the subject of that dare might have been. He could do this.

Castiel took a deep breath, and just as the guy walked passed him, he asked, "Would you like to go out with me?"

The guy didn't even look up from his phone. For a moment, Castiel thought he was just going to keep walking. He _hoped_ that he was just going to keep walking. He'd done what he had to do, and if he was able to avoid the aftermath of that, well then that was be amazing. It would make this so much less awkward.

Maybe he hadn't noticed him. Or maybe he had and he didn't think that it was worth his time for him to stop. Which was understandable. Because if Castiel looked like that guy, he wouldn't just stop for guys that looked like him either. That was what he wanted to happened, but no, no such luck. Because Castiel wasn't particularly lucky as fate would have it.

Because about three feet from Castiel the guy paused and looked up. Castiel's heart nearly gave out as green eyes met blue. And oh my god, his eyes just added to the whole package. If the guy wasn't standing an arm's-length away and staring at him, Castiel might have fanned himself.

The guy reached up and pulled one of his earphones out.

"You say something?" he asked, arching an eyebrow. And oh god, even _his voice_ was attractive. How was that _fair_?

Castiel blanched for a moment, the guy's ethereal beauty causing him to lose all his wits temporarily and forget that he'd asked him a question, before he rushed out, "Would you like to go out with me?"

The guy tilted his head and stared at him for a long moment, and Castiel almost apologized and took it back, but then a slow smile spread across his face. Castiel could have swooned right then and there. Because standing this close to him, Castiel was now able to come to a conclusion. This was by far the most attractive person he had ever had the pleasure of standing near in his entire life. This would go down in the history books for sure.

"Direct," the guy said with a grin. "I like it. Sure, I'll go out with you."

Castiel stood frozen in shock for a moment while his brain caught up. For a moment he thought that he must have dreamed it. Because in no world would that have actually just happened to him. There was no way that this guy had just said yes. No way. Not possible. Because things like that didn't happen to him. But there he was, the most attractive person Castiel had ever breathed the same air as, still standing there and smiling at him. And very much waiting for a response. So of course, being the level headed and eloquent person he was, Castiel handed the situation with the amount of elegance and poise that it warranted.

"What?" he blurted. He quickly realized how that must have sounded, and amended with, "I mean, wait, you will?"

The guy flashed him a toothy grin and nodded. "Yeah, why not? You free tonight?"

Castiel's mouth dropped open. This was supposed to be a _joke_. Some stupid dare. He never anticipated that someone would actually say _yes_. Let alone someone as attractive as this guy. This attractive guy who was trying to make plans for _tonight_. Like this same day. In a few hours. That tonight.

He threw a helpless glance over his shoulder at Charlie, who was watching the whole encounter intently. Like seriously, she was watching them like all she needed was a bucket of popcorn and she'd be set. He widened his eyes in fear as if to say 'What do I do?' Her eyes were just as wide and she just shook her head helplessly; being no help whatsoever. Meaning unfortunately, it looked like Castiel was on his own with this one. Even though it was _all Charlie's fault _that he was in this situation to begin with.

The guy followed Castiel's gaze and gave Charlie a small smile and a wave. She waved back awkwardly, and then quickly focused her attention on her phone, pretending that she was not in fact committedly eavesdropping to ever word.

Castiel turned back to the guy, with the full intention to tell him that he had just been kidding. That it had been a dare, and he never expected him to say yes. He had his apology all set and ready to go. But the guy was still kind of smiling at him, and then without his agreement he felt himself start nodding. "Tonight is fine," he squeaked. _What!?_

He could have smacked himself. Because one, what the hell was he doing? And two, since when did he ever _squeak._

The guy grinned. "Awesome. Should I pick you up, or do you wanna meet somewhere?"

"Um, meeting somewhere is fine," Castiel answered awkwardly.

Because he had somehow convinced himself in the last twenty seconds that it would be rude to take it back now. Especially after the guy—and now Castiel— had already agreed. But at the same time, he recognized that it was also be rude to let this guy believe that he'd meant it. Overall, he had literally no idea what the hell he was even doing. But now he appeared to be in too deep and was just rolling with it.

The guy nodded. "Cool, cool. Oh," he stuck a hand out, "I'm Dean by the way." He chuckled. "Dean Winchester." And was it possible for someone to have an attractive name too? Because he was pretty sure _Dean Winchester_ was the best name he'd ever heard. And oh my god what was wrong with him?! _Snap out of it, Castiel!_

Castiel shook his hand, continuing to just stare at him. (Like a creep.)

"And you are?" Dean prompted with a simper. And this guy really needed to stop smiling at him otherwise Castiel was going to melt into a puddle at his feet.

"Oh, right," Castiel said sheepishly. _Smooth Novak. Gabriel would be so ashamed of you right now._ He could feel a blush working its way up his neck. "I'm Castiel Novak."

Dean cocked his head to the side. "Cas-ti-el," he said pronouncing each syllable with care. Castiel didn't want to admit that hearing his name on the man's lips sent a shiver down his spine. "Kinda a mouthful, don't cha think? You got a nickname or anything?"

Castiel shook his head.

"Mind if I call you Cas?" he asked. Castiel shook his head again, to let him know that no, he didn't mind. And when did he suddenly lose the ability to form coherent sentences? And to think, the fact that he'd always been so well spoken was one of the things he prided himself on. "Okay, Cas." Dean grinned. "I like it. Suits you."

He may have liked the way that sounded on his lips even better. _Cas. _His mother certainly wouldn't have approved of that.

"So Cas," Dean said. "Anything in mind for our date? Or did you wanna keep it like a spontaneous we'll find something to do sort of thing?"

Castiel froze. There wasn't even supposed to _be _a date, (even though his heart might have skipped a beat hearing Dean refer to it as so). He hadn't come up with a plan. And why was he even still going along with this? The whole thing was very confusing. "Spontaneous," he answered.

Dean nodded. "Awesome," he said. "Give me your phone so I can give you my number."

Castiel handed over his phone obediently. Dean tapped at it for a few moments and then gave it back. "All set. I texted myself too, so now I have your number," he said. "Wanna just meet here later? Say around seven?"

Castiel found himself nodding yet again. It was like this guy showed up and turned his resolve to jello.

Dean flashed him a grin. "Awesome. Okay. Well, see you later, Cas." Then he put his headphone back into his ear and continued walking away down the path like nothing had happened. Like Castiel wasn't in the midst of questioning why he'd even bothered getting out of bed that morning.

Castiel stood frozen for a few moments, watching Dean's retreating form until he disappeared from sight. Then slowly, he turned to face Charlie. She was staring at him with wide eyes and an open mouth.

Castiel raised his hands up in the air. "What the hell!" he cried.

Charlie shook her head furiously. "I have no idea! Oh my god! Why did you agree to go out with him?" she asked.

He made a sound of aggravation. "I don't know! He's was just so good looking. And it would have been rude to take it back. And he seemed really nice. . ." He went and plopped down back on the bench next to her. "Did I mention that he was good looking?" he asked weakly.

Charlie hummed thoughtfully. "Believe me, buddy. I noticed. I may like girls, but dude was like a Greek god. Geez Louise." He found himself nodding in agreement for a moment before he snapped out of it and remembered that he now had a date tonight with a guy he had asked out as a dare.

He groaned. "What do I do?" he asked helplessly.

"Oh, no Castiel. You don't come to me for dating advice. You come to me when you don't understand a pop culture reference that someone made. You come to me when you want to talk about nerdy crap. You come to me for computer help. You do not come to me with boy problems. Because first of all, I'm playing for the other team, and second of all, I am single with a capital S." She patted his knee. "You're on your own here. Sorry champ."

He slumped against the back of the bench, defeated.

"Well," Charlie said, "at least he's hot. It could have been worse. He could have been old and gross."

Castiel groaned. Yes, he supposed, it could have been worse. But it was still pretty bad. Either way, it looked like he had a date with Dean Winchester tonight.

"So," Charlie said after a few moments of silence, "game's over, right?"

Castiel snorted. "Yes, Charlie. The game is over."

* * *

Castiel spent the rest of the day pacing back and forth in Charlie's room while she lay on the bed with a comic book in her lap watching him. He was freaking out. Plain and simple. He had absolutely no idea what he should do about Dean. _Dean_. He almost felt guilty just thinking his name. He shouldn't even know his name. He shouldn't have even spoken to him. They should have had no effect on each other's lives whatsoever. And now look at him. Running a hole in the middle of Charlie's carpet because he'd asked a guy out on a dare and hadn't expected him to agree.

A million different things were whirling through his head at once.

Should he just not show up? No, that would be rude. And a waste of Dean's time. But wasn't it also rude to go on the date when he hadn't meant it? If it was under different circumstances he would be _thrilled_ to be going on a date with Dean Winchester. He was extremely attractive and had seemed nice from their brief encounter in the park. But he felt like he was taking advantage of Dean by deceiving him. Everything was all muddled and confusing. And Castiel didn't know what to do.

Maybe he should show up and tell Dean that it had all been a dare and then take it from there? No. Then he would have gotten ready and got all the way there only to turn around and go home? Should he just text him and tell him? No. That wasn't something you said over a text. Call? Maybe. But honestly, he knew that he was way too chicken to do that. Which aggravated him because next to nothing scared him. What the hell was it about this guy that was messing him up this way?

Why had Dean even agreed to the date at all? By the looks of him, he definitely did not have a shortage of date offers coming in. Like really, _look at him_. Wait, what if he was weird? What if he was really weird and like ate dirt or something. Or what if he was a serial killer? Oh my god he could have a date with a serial killer tonight!

But even then he knew that he was being stupid. He was just nervous and trying to talk himself out of going. It was pathetic honestly. Truly pitiful. His father would be so ashamed. He needed to grow up and deal with this.

Because Castiel was an _adult_. He was going off to college next year, and venturing out into the world as a real person. He needed to learn to solve his own problems. And really if you thought about it, having a date with an extremely attractive person wasn't actually a problem. Expect for when you considered how that date came to be, and then there's your problem. Because in any other circumstance, Castiel would be beyond thrilled, but in this case he couldn't help but feel guilty about the whole thing. And to be completely honest, there was a part of him that was still thrilled. Because the guy had said _yes._ _To him._ _Castiel Novak_. If that wasn't an ego boost, he didn't know what was.

But that was the part of him that wasn't a particularly good person.

Eventually, Charlie got so sick of listening to his freak out that she told him to shut the hell up and get out of her house, because his date started in an hour and he still had to go home and change. Because what he was wearing was more suited for a library than a date.

Castiel glanced down at his sweater protectively. It was red and the sleeves were just long enough that he could tuck his hands inside of them—a nervous habit he had. "I happen to like this," he said, frowning.

She rolled her eyes. "I know you do. And Mr. Perfect must—"

"Dean," he corrected.

Charlie narrowed her eyes. "—not have been too appalled by it since he agreed to go out with you. Even still, you should go change. He already saw you in that outfit today." He frowned and grumbled about how it wasn't even supposed to be a date, but agreed nevertheless.

But just to spite her, he went home and changed into a different sweater; a blue one that he'd been told brought out his eyes. He took a picture of himself in it and sent it to Charlie just to annoy her. She texted back with a reply that said, _You're hopeless, Castiel_. He smirked and typed out a reply, pleased with the reaction he'd elicited from her.

Then he left his house and headed toward the park. He spent his walk to the park thinking of more ways that he could potentially annoy Charlie, all the homework that he needed to get done before heading back to school next week, what he and Charlie could do tomorrow to fight the boredom that plagued their days. Anything and everything that helped him take his mind off of Dean and their accidental date.

He'd given up his on freak-out, because really, what was the worst that could happen? Why had he even been freaking out about it at all? Because really, it wasn't a big deal. It was just a date. So this was Castiel's game plan: go on the date, enjoy the hell out of it, and try not to fall in love with perfect Dean Winchester because he'd probably never see him again after tonight. Because Dean probably wouldn't even have a good time. Then there wouldn't be a second date, and he could just forget about the whole thing. All he had to do was get through a few hours of feeling kind of guilty and trying not to literally drool over Dean's impressive face and physique, and then it would all be over. Then in a few years he and Charlie could look back on this and laugh about how freaked out Castiel had been. It would make a good story. And that was all it would make—a story. Because there certainly _would not_ be a second date.

Castiel got to the park a few minutes before seven, and was surprised to see Dean already there waiting. He was sitting on the bench where Charlie and Castiel had been earlier, reading a book. His stomach turned uneasily. He'd been able to distract himself on his walk here, but now it was actually real. Actually real and sitting on a bench reading a worn paperback. And here he thought he would have had a few minutes to prepare himself before Dean showed up. But apparently not, because Dean was even more prompt than he was. He swallowed hard and approached him slowly. Dean still hadn't noticed his presence when he was nearly directly in front of him. He cleared his throat.

He looked up and smiled when he saw Castiel standing there.

"What are you reading?" Castiel asked in lieu of a greeting, because apparently he'd forgotten all of his manners. His mother would have been so disappointed.

"Oh," Dean said glancing down at the book. He held it up so Castiel could see the cover. _Cat's Cradle_ by Kurt Vonnegut stared back at him. _Oh no,_ he thought desperately, _he's well-read too_.

Dean smiled sheepishly and tucked it into his jacket. "One of my favorites."

Castiel nodded. "I liked it as well."

Dean just stared at him for a minute, smiling. It made Castiel stomach turn uneasily once more. He just oozed genuineness. It made Castiel feel like an ass all over again. He pushed it down. He just had to get through the next few hours and it would all be fine.

Dean stood up from the bench. He was wearing different pair of jeans and a fitted black V-neck T-shirt under the same leather jacket. And he looked damn good. "Well, shall we, Cas?" he asked with a sweeping arm gesture.

Castiel swallowed hard and nodded. "We shall."

"I parked over here if you wanna follow me," he said pointing across the street. Castiel nodded and followed along behind him, doing his best not to think about all of the things that were wrong with getting in a stranger's car. Dean brought him over to an old looking car, and Castiel wasn't much for cars, but even he could tell it was nice.

"This is yours?" he asked, a bit awestruck.

Dean smirked. "Yes sir," he said running a hand over the hood. "This is my baby."

He furrowed his brow. It seemed like an odd car for such a young guy to have. Well, at least he thought Dean was young. He looked young, but he could just have one of those faces. Wait. What if he was like forty-five? Castiel couldn't go out with a forty-five year old he was still in high school. _Oh my god_. _Castiel pull it together, _he scolded himself. He doubted that Dean was actually forty-five. Maybe he just came from money or something.

"She's beautiful," Castiel noted.

Dean inclined his head in agreement. "My dad gave her to me when I graduated high school. Best damn graduation present ever, if I do say so myself." So the car was a gift.

"You graduated?" Castiel asked.

"Going on two years now," he told him. And Castiel exhaled in relief. Alright, he was only twenty; and not in fact, forty-five. "You?"

"This is my last year. I'm a senior," he informed him.

Dean grinned and nodded. "So close to freedom. You know what you wanna go to school for?"

"Medicine," Castiel said matter-of-factly. "I want to be a doctor."

Dean whistled. "Damn. Look at you, Dr. Novak. It has a nice ring to it."

Castiel ducked his head, trying to hide a smile. "And you?" he asked.

"Engineering. Mechanical." He shrugged like that wasn't a big deal.

"That's impressive," Castiel nodded. And it was. _And he's smart. Kill me. Kill me now._

Dean cocked his head. "Ya think?"

"I know."

Castiel was mentally keeping a list of everything he had learned about Dean Winchester so far; wears leather jackets, likes Vonnegut, likes classic cars, agrees to dates with strangers he met in the park, is incredibly attractive, is intelligent, is modest, _is incredibly attractive_. And unfortunately, Castiel couldn't find anything he didn't like about that list thus far.

"So did you have anywhere in mind for tonight?" Dean asked. "If not, I have a place."

"I'm sure whatever you want to do is fine," Castiel said.

"Awesome," Dean said. He opened Castiel's door for him. "Let's go. Oh, by the way, Cas. That color looks really good on you. Brings out your eyes." He gestured to Castiel's sweater.

Castiel smiled smugly. He made a mental note to text Charlie later and brag about his sweater. Hopeless his ass. A hot guy had complimented him on it.

Over the course of the ride Castiel watched as Dean whispered sweet nothings to his car and ran his hand lovingly over the dashboard. For anyone else that would probably be extremely strange behavior. But for Dean it just fit. It just seemed to make sense for him. Castiel wasn't really sure what that meant.

Dean brought Castiel to a tiny dinner. Which made Castiel relax considerably. Nothing fancy, nothing big, nothing that weighed too heavily on his conscience.

When they walked in the bell above the door chimed, alerting the staff to their presence. A tall gangly guy looked up from behind the counter at the sound and broke out into a grin.

"Dean!" he called, ambling toward them in a way that was much akin to a golden retriever. "Is this the big date?" he asked, eyeing Castiel amicably.

Dean grinned and looked over at him. "Yeah Garth, this is him," he said. "Garth, Cas. Cas, Garth."

Castiel, remembering his manners this time, stuck a hand out. "Nice to meet you," he said.

"Oh, come 'ere you!" Garth cried disregarding Castiel's hand completely, and instead pulling him into a hug. Castiel stiffened and shot Dean a helpless look, wondering if it was normal behavior for the staff of this establishment to embrace patrons. Dean just smiled and shrugged.

"Garth!" a gruff voice shouted. "Stop trying to hug Dean's date to death, ya idjit!" Castiel looked up from underneath Garth's arm and found an older man in a trucker hat with a beard walking toward them. "You got tables to bus, busboy. Get the hell back to work. I ain't paying you to stand around hugging people." Garth dropped his arms immediately, and Castiel took a small step back.

Garth swallowed hard and saluted him. "Sir, yes sir, Mr. Singer, sir. Sorry for being such an idjit, sir." Garth bowed his head and retreated back to where he'd been wiping down the counter. Mr. Singer, Castiel's savior, shook his head watching him go.

Mr. Singer inclined his head to Dean in greeting, and then turned to Castiel.

"Nice to meet cha," Mr. Singer said shaking Castiel's hand. "Bobby Singer. This is my diner."

"You too, sir," Castiel said. Only finding it a little strange that everyone here seemed to know Dean, and also know who Castiel was supposed to be. Maybe Dean was a regular here?

Bobby narrowed his eyes at him. "None of that sir crap, alright? Garth only does that 'cause he's weird. Bobby'll do just fine." Castiel nodded quickly. Bobby studied him for a moment, and then gave a curt nod. Maybe of approval? He wasn't really sure. The man was kind of intimidating. Bobby shifted his attention to Dean. "And you. Don't you spend enough time here as it is? Gotta come back even when you ain't working too?" Ah, so that's how everyone knew Dean.

"You know me," Dean drawled. "I just love your burgers."

"And you can get 'em at home." _Home?_

"Is this your father?" Castiel asked. They didn't have the same surnames, but then again that didn't really mean anything.

Dean shook his head. "No, but he's pretty much as good as. Family don't end with blood like he's always saying."

Castiel nodded, although he didn't really understand. Then he froze. Dean took him to his place of business. Where it seemed like some of his friends and family worked. Why would he have done that? Was that normal first date behavior? Castiel didn't think so. What was he thinking? Another round of guilt swirled in Castiel's gut.

"Alright, go grab yourselves a table. Table three is open, Dean." Bobby said waving them off.

Dean frowned. "But that's—"

Bobby grinned. "Jo's section. I know." He winked.

Dean sighed. "Alright, c'mon Cas." He took a hold of Castiel's elbow and led him to a table toward the back of the restaurant. Heat coursed through his body when Dean touched him. He pushed that down too.

"What's wrong with Jo?" Castiel asked when they sat down.

"Yeah Dean," a new voice said coming up behind him. "What's wrong with Jo?" Castiel turned and found a petite blonde standing at the edge of their table. She had a notepad in one hand, and her other hand rested on her hip.

Dean smiled. "Hiya, Jo. How goes it?" _Oops_. He turned back to Castiel. "And nothing really. She just loves to bust my balls."

Jo smiled at him sweetly. "This your date?" Castiel frowned. Had he told _everyone _he knew about the date?

"Yeah. This is Cas."

Jo gave him a once over. "Well Cas, I'm not sure how Dean tricked you into going out with him tonight, but it's very nice to meet you. You look a lot nicer than most of the trash he hangs around."

Dean made an annoyed face. "Oh hey, c'mon!"

"I actually asked him out," Castiel informed her. Another stab of guilt.

Jo raised an eyebrow. "Oh, yeah? And I was just kidding. He doesn't usually bring the trash here. So you must be special or something." She winked. Completely unaware of the inner turmoil Castiel was going through at her comment. She reached into her apron and pulled out a pen. "What can I get you boys?" she asked clicking it open and readying it on her pad.

"I'll have a burger and coke," Dean said without even glancing at the menu.

Jo rolled her eyes. "What else is new. And you, Cas?"

"Um, the same I guess." Dean did work here. He would know what was best. And Castiel had never met a burger that he didn't like.

Jo scribbled on her pad and then flipped it shut. "That'll be right out."

Dean scoffed. "I highly doubt that. I happen to know for a fact that Ash is working the grill, so I'll be expecting our food sometime next year."

Jo sighed. "Well sorry, Dean." Her tone was dripping with sarcasm. "It's your night off, and not everyone can be a master grills man like yourself." Dean looked like he wanted to reply—maybe complain about her use of condescension, but with that Jo walked away and disappeared into the kitchen. Dean glared after her for a moment.

"So, you work here," Castiel said.

Dean turned back to look at him and nodded. "Yeah. Me and my brother, Sam." So he had a brother too. And a not-father father "Like I said earlier Bobby's like our second dad. Since our real dad wasn't really around much when we were kids."

"Oh, why was that?" Castiel could have smacked himself once the words left his mouth. He had absolutely no right to be prying into Dean's life like that. His mother had taught him better than that.

But it didn't seem to bother Dean. "Our mom died in a fire when Sam was only six months old. She was the love of my dad's life. After she died he just lost it. He disappeared for months and left us with Bobby. We still don't know where he went." Dean's eyes glazed over for a moment. Like he was reflecting. "When he came back, he wasn't the same. He just kinda checked out. He didn't stick around. Just dropping by every couple months. Sometimes for holidays and birthdays, sometimes not. So me and Bobby raised Sam pretty much."

Castiel was sure why Dean had told him all of that. They barely knew each other. It made him feel guilty for about the fifteenth time that day. But maybe he was just an open individual. He wasn't really sure. But learning that Dean had been one of his brother's caretakers, that he'd cared enough to take care of him in his father's stead; well that only made Castiel like him more.

"I'm sorry," he told him sincerely.

Dean gave a sort of sad smile. "I hated him for a long time, but now that I'm older I think I understand him. I couldn't imagine losing the love of my life like he did. Things aren't great with us now, but he tries."

"Like giving you that car for your graduation."

Dean smiled, a happy smile, at the mention of his 'baby'. "Yeah. The Impala was kinda like a peace offering."

"I see," Castiel said nodding.

Dean's gaze shifted to behind Castiel's head. He grinned bigger and brighter than Castiel had seen yet. "And speaking of family. Look at this little bitch."

A boy about sixteen was walking by carrying a stack of dirty plates. He frowned at Dean. "What did I ever do to you?"

"Ah, I'm just kidding Sammy. You know that." He leaned out and ruffled the boy's hair. So this was his brother, Sam. "Hey, meet Cas."

Sam grinned at Castiel. "Hey, so you're Cas. Nice to meet you."

"And you as well."

Sam gave Dean a look that Castiel couldn't quite decipher, and Dean shot him a glare. "Okay get back to work, bitch. Can't you see I'm on a date?" But there was no animosity in his words. Just genuine brotherly affection. Castiel knew a thing or two about that.

"Jerk," Sam grumbled walking away.

Dean watched Sam go with a goofy smile on his face. A moment later Jo came bustling out of the kitchen and delivered their food.

"What about you?" Dean asked, digging in. "Enough about my family sob story. What was it like for you growing up?"

Castiel took a sip of his soda. "My upbringing was rather boring actually. My parents are both very religious. I went to church a lot."

"That where the weird name come from?" Dean asked stealing a fry off of Castiel's plate and popping it in his mouth. Even though he had a whole plate of his own.

"Castiel, Angel of Thursday," he replied.

"You like it?" Dean asked.

No one had even asked him that before. "I used to hate it," he admitted. "I always resented that my parents couldn't give me a normal name. It led to some teasing in school. But now I've come to like it. It's unique, and it's mine. I've accepted it."

"So, are you not super into religion?"

"It has its merits. I do believe in God, but I'm pretty sure he's not paying much attention to us. Were on our own you might say."

Dean nodded. "I never really got into that religion stuff. I don't like the idea of destiny and fate and all the crap. I'm a man of free will." He grinned.

Castiel was really trying not to like this guy.

"So besides the church stuff, things were good for you?"

Castiel thought for a moment. "They were alright. My mother was very strict. I had a very proper upbringing. My father mostly went along with whatever she thought was best."

"I can tell by the way you talk. You sound like a sixty year old English professor." Dean smiled. Somehow, Castiel could tell that he'd meant it as a compliment.

He gave his own small smile. "Thank you."

"Got any siblings?" Dean asked, mouth full. Normally Castiel would have found that to be disgusting. However, he didn't seem to mind much now. It was still gross, but at the same time inherently Dean. And he wasn't bothered by it.

"Just one, Gabriel. And he is a menace." Castiel smiled fondly.

"Oh yeah? How so?" he asked, intrigued.

"He's quite fond of pranks. He's a real trickster you might say."

Dean laughed. "That's kinda like me and Sammy. We get into it sometimes. Itching powder in each other's underwear. Putting crazy glue on stuff and waiting for the other one to pick it up. Stupid shit like that. What kind of stuff does Gabriel do?"

"Well, most recently he took my entire bedroom set and moved it to the roof."

Dean nearly choked on his drink. He swallowed and then coughed a few times. "Huh. This guy doesn't mess around, does he?"

"No," Castiel agreed. "He does not."

"I'd like to meet this guy."

Castiel smiled softly. "Be careful what you wish for."

And then, guilt, guilt, guilt, and more guilt. He was joking about wanting to meet his family.

Much to Castiel's dismay, the not-real-date date was going extremely well. While he and Dean didn't have many things in common, that didn't stop them from being able to get along. They didn't have the same taste in music at all. Dean swore by Classic rock, while Castiel would rather listen to classical music. Where Dean was an avid Vonnegut fan, Castiel had only liked it in passing. Dean was very into cars, whereas Castiel knew little to nothing about them; and despite being a senior in high school he didn't even have his license yet. At that, Dean gave him a disapproving look and offered to teach him to drive in his car. _In his beloved car._ Castiel hadn't known the guy long, but even he could tell that he loved that car like a child. Hell, they weren't even studying the same things in school.

But despite all of this, there was never once a lull in their conversation. Not a single awkward pause, or a tense moment. The only time either of them stopped talking was to stuff their mouths with their food—which was surprisingly good for diner food—and even then they were most likely listening to the other talk. And even after they finished their dinner, Dean insisted they order dessert. He was a rabid pie lover apparently, and Bobby's diner had the best in town. Jo brought them out apple pie, and set it down on the table, giving Castiel a meaningful smile. He found himself smiling back.

Castiel was actually having a really good time. It was the best date he'd ever been on, hands down. And it was the most he'd ever connected with a virtual stranger in his entire life. And the more they talked, the more he felt like he knew Dean. Like he'd known him for a while. The only problem was that it didn't fell like it was real because of how they'd gotten here. Castiel was having fun, but he couldn't shake the feeling of guilt. And with each passing moment that he enjoyed himself, the guilt grew.

And the worst part, the absolute worst, was that as Castiel watched him eat—which wasn't a particularly pretty sight might you, he realized something horrible. He could probably fall in love with Dean one day. Which was exactly what he didn't want to happen.

He felt sick. Dean noticed.

"Everything alright over there, Cas?" he asked looking concerned.

He nodded. "Everything is fine." _I asked you out as a dare_.

"Are you sure? You're looking a little green around the gills. Your pie okay?"

"The pie is fine, Dean," he assured him. _I feel awful about it. _

"Alright. If you're sure." He looked a bit skeptical.

"I am. Thank you, Dean." _I think I could end up having real feelings for you_.

They finished their dessert. It was very good after all.

Soon they were done with their meals, and it was time to pay. Jo brought over the check and Castiel watched Dean reach for his wallet.

"Hey, stop. I'll pay. I'm the one who asked you out remember?" Castiel said hurriedly. He wasn't going to make the guy pay for a dare. It wasn't right.

Dean grinned, and waved him off. "Nah, don't worry about it. My treat." He handed Jo some bills, and she patted his head and walked away towards the register. Then he grinned at Castiel. "You can always get the next one."

Castiel's stomach sank.

"Night, Dean. Cas," Jo called over her shoulder.

"Night, Jo," Dean called.

"Goodnight," Castiel said quietly.

Dean and Castiel got up from their booth, and shrugged on their coats in preparation for heading back out into the cold. Dean called a goodnight to the rest of the restaurant, and then they walked outside and back to his car. Castiel gave Dean directions to his house. And for the entirety of the ride, Castiel sat in the passenger's seat feeling like actual trash.

When pulled up in front of Castiel's house Dean cut the engine.

He unbuckled his seatbelt, and turned to face Castiel. He smiled. "I had a good time tonight, Cas."

Castiel bit his lip. "I did too," he confessed.

Dean grinned. It lit up his whole face. "I like you, Cas. Would you be interested in doing this again sometime?"

"Yes," he said before even thinking about it.

Dean's smile grew. "Awesome." He leaned toward Castiel, and Castiel found himself leaning back; moving to close the short distance between them. In that moment all he wanted to do was kiss him.

But at the same time he just felt like he was taking advantage of Dean. He was torn between whether or not he should tell him that he'd only asked him out as a dare. Because he felt wrong about starting something under false pretenses. But on the other hand, he didn't want to ruin it before it even started. Because he liked Dean a lot more than he'd originally anticipated. A lot more than anyone else he'd liked before actually. They might have just met, but somehow Castiel felt like they just _clicked._ So really, Castiel was just a big fat coward who was afraid of how Dean was going to react if he did tell him. And that he'd get mad and never want to see him again.

And on a shallower note, he might never get the opportunity to kiss someone this attractive ever again; and if that was the case shouldn't he go for it? Carpe diem and all that. Dean was way out of his league after all.

And that wasn't to say that Castiel was not attractive, because he was. And he wasn't saying that to be vain either. It just simply meant that he'd been told by various different people that he was good looking. But Castiel was attractive in a way that his facial features came together in a manner that created something aesthetically pleasing. And he'd been told that his eyes helped. They were a rather intense shade of blue as it was.

But Dean on the other hand was attractive in a way that the planets must have aligned, and galaxies must have been born and died in order for his otherworldly beauty to come into existence. And if Castiel tried hard enough he thought that he might have been able to chart constellations in the freckles that dotted his skin. But he never really was good at Astronomy.

Their lips were mere inches away now, and Castiel watched as Dean's eyes slipped shut. All he wanted was to just move forward and press their lips together. But in the end, his need for an honest foundation and just general humanity won out. Damn his decent upbringing and his parents raising him to be a good person.

So he stopped himself. And that was much harder than you might think. Because if you had been there. If you had seen the way that Dean was looking at him. You probably wouldn't have been able to pull away. It was most likely only due to his strict upbringing and various exercises in self-restraint that he was even able to at all. So he could thank his mother for something.

"Dean," he said quietly. Their lips were only centimeters apart.

"Yeah, Cas?" he asked without opening his eyes.

"I need to tell you something."

Dean pulled back. "What's up?"

Castiel swallowed hard, and prayed that if Dean did punch him in the face after this that he wouldn't get any blood on his sweater. It was his favorite after all. "Um right before I asked you out me and my friend Charlie, the girl I was with at the park, we were playing this stupid game."

"What game?" Dean asked.

"Um, Dare?"

Dean nodded. "Go on."

"And you were one of the dares," he said quickly.

"What?"

Castiel took a deep breath. "She dared me to ask the next guy out that I saw and that was you. It was just supposed to be some dumb thing. But then you said yes, and I didn't know what to do, and now I realized that I actually like you. And I'm so sorry—"

And then he stopped because Dean wasn't getting mad. He wasn't upset. He wasn't ready to punch Castiel in the jaw. He was _laughing_. Wait, what the hell?

"I don't understand," Castiel said slowly. "Why are you laughing?"

Dean was hunched over holding his gut. "I'm sorry," he said between laughs. He held up a hand. "Hold on." And Dean really did have a nice laugh, but seriously what the hell was funny?

Castiel waited while Dean composed himself, apprehensive and confused. And then Dean said the last thing that Castiel was expecting to hear.

"I knew the whole time," he said trying to suppress a smile.

Castiel's eyebrows shot up to his hairline. "Come again?"

"I only said yes to fuck with you man. I saw you and your friend doing all that weird shit in the park. I was sitting a little bit down the path reading. I figured you were playing some weird game," he explained. "So I wasn't really surprised when you asked me out. I was, however, surprised when you didn't back down after I said yes. So, I figured, hey why not this guy's cute. So I kinda just rolled with it. Which apparently is the same thing you did. And I'm happy I did because I actually like you man. I didn't even tell my family that it was fake. I figured I'd see how it went."

He knew. He knew the whole time. How was this Castiel's life?

"Oh my god," Castiel breathed. "I was freaking out all day! I felt so guilty!" But it felt like a weight had been lifted off his chest.

Dean laughed again. "Sorry man that's what you get. I'm actually pretty surprised that you told me. I figured it was gonna be like one of those dramatic things that end up coming out like years into our relationship and cause an uproar."

"Wait, so you would have wanted to see me again even if I hadn't told you?" Castiel asked narrowing his eyes.

Dean nodded. "Yeah, like I said. I like you. And I doubt you would have kept up the charade that long if you weren't into me." He winked. He honest to god winked at Castiel. And he might have died a little.

Castiel kind of faltered at that. "Oh my god," he said slowly. "You're an asshole."

Dean laughed at that. "Hey!" he protested. "I'm not the one who asked a guy out as a dare and went through with it!"

Well, he had him there. "I guess you have a point," he conceded.

"I guess were both just a couple of assholes," Dean said, leaning in close. He closed the distance between them, and kissed him. And kissed him. And kissed him. And kissed him. And kept kissing him, until finally Castiel pulled back.

"Wait," he breathed close to Dean's mouth. "So you aren't upset with me?"

Dean shook his head. "Hell no, Cas. If anything I think it gives us a good story for how we met." He grinned crookedly.

Castiel raised an eyebrow. "Does that mean a second date is still on the table then?" he asked.

Dean laughed and nodded. "Come here you," he said, and pulled Castiel in for another kiss of many more to come.

* * *

A year later, and they were sitting on the same bench that Castiel and Charlie had been sitting on the first time that he'd ever seen Dean. And they were playing Dare.

Dean nudged Castiel with his shoulder, and pointed to a man walking down the pathway. "I dare you to ask that guy out on a date," he said.

"Careful," Castiel warned playfully, "I might fall in love with him."

Dean leaned down and kissed his temple. "He couldn't be that lucky."

**AN: Thanks for reading! Feedback appreciated! **


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